CONTENTS

CONTENT Abstract /Summary Introduction Procedures Results Discussions Conclusions References

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ABSTRACT

The experiment was carried out to identify 12 compounds (compound A to compound L) by using the knowledge of UV-Vis and IR Spectroscopy. In progressing of the experiment, we obtained and observed the IR spectrum by using UV-VIs and FTIR spectroscopy. From the data collected, we can identify all of the compound A to L. the results showed that compound A is ethanol, compound B is ethanal, compound C is ethanoic acid, compound D id ethyl ethanoate, compound G is benzene, compound H is toluene, compound L is benzoic acid, compound J is bromoethane and compound K is ethane. We are successful in identifying the all compounds.

INTRODUCTION
There are several ways in finding the type of compounds. In this experiment, the Ultraviolet (UV)-Visible and Infrared (IR) spectroscopy will be use to find the functional group of the compound sample. The UV-Visible spectra of organic compounds are associated with transitions between electronic energy levels in which an electron from a low-energy orbital in the ground state is promoted into a higher-energy orbital. The transition occurs from a filled to a formerly empty orbital to create a singlet excited state. The UV-Vis absorption spectroscopy is the measurement of the reduction of a beam of light after it passes through a sample or after reflection from a sample surface. Absorption measurements can be at a single wavelength or over an extended spectral range. Ultraviolet and visible light are strong enough to promote outer electrons to higher energy levels, and UV-Vis spectroscopy is usually applied to molecules or inorganic complexes in solution. The UV-Vis spectra have broad features that are of limited use for sample identification but are very useful for quantitative measurements. The concentration of an analyte in solution can be determined by measuring the absorbance at some wavelength and applying the Beer-Lambert Law. Beer-Lambert law Theory The Beer-Lambert Law method is most often used in a quantitative way to determine concentrations of an absorbing species in solution,

where : A= the measured of absorbance I0 = the intensity of the incident light at a given wavelength I = the transmitted intensity l = the path length through the sample c = the concentration of the absorbing species = extinction coefficient absorbtivity
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Since the UV-Vis range spans the range of human visual acuity of approximately 400 750 nm, UV-Vis spectroscopy is useful to characterize the absorption, transmission, and reflectivity of a variety of technologically important materials, such as pigments, coatings, windows, and filters. This more qualitative application usually requires recording at least a portion of the UV-Vis spectrum for characterization of the optical or electronic properties of materials. The energy associated with a given segment of the spectrum is proportional to its frequency. The bottom equation describes this relationship, which provides the energy carried by a photon of a given wavelength of radiation.

V = frequency C = velocity of light (3 x 1010 cm/s) = wavelength

E = Energy h = Plancks constant V = frequency

Infrared (IR) spectroscopy is one of the most common spectroscopic techniques used by organic and inorganic chemists. Simply, it is the absorption measurement of different IR frequencies by a sample positioned in the path of an IR beam. The main goal of IR spectroscopic analysis is to determine the chemical functional groups in the sample. Different functional groups absorb characteristic frequencies of IR radiation. Using various sampling accessories, IR spectrometers can accept a wide range of sample types such as gases, liquids, and solids. Thus, IR spectroscopy is an important and popular tool for structural elucidation and compound identification.
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In IR radiation, energy to induce electronic transitions is weak compare to UV. Therefore there is a restriction for absorption of IR where a compound with small energy differences in the possible vibrational and rotational states only can be detected. For molecules to absorb IR, the vibrations or rotations within a molecule must cause a net change in the dipole moment of the molecule. The alternating electrical field of the radiation interacts with fluctuations in the dipole moment of the molecule. Radiation will be absorbed if the frequency of the radiation matches the vibrational frequency of the molecule then causing a change in the amplitude of molecular vibration. Basically, the IR spectroscopy works like an UV-VIS spectroscopy. The difference is only on the radiation absorbed. In the IR spectroscopy, the sample will absorbed the IR beam while in UV-VIS the sample will absorbed the UV-VIS beam. The infrared of the spectrum is collected by passing a beam of infrared light through the sample. From this, a transmittance or absorbance spectrum can be produced, showing at which IR wavelengths the sample absorbs. Analysis of these absorption characteristics reveals details about the molecular structure of the sample. A graph will be plotted using the absorbance detected. For an example:

This chart shows that various kind of band can be detected or observe based on the absorption of the sample exposed to the IR beam. When there is absorption, a region which is a curve can be observed. Each region is referring to its own functional group where the functional group has specific range of wavelength number. When we know the functional group of the sample, we can identify the sample given. An example of functional group with the range of wavelength number: Function Range al Class (cm )
-1

Intensity str

Assignment CH3, CH2 & CH 2 or 3 bands

Range (cm-1) 1350-1470 1370-1390 720-725

Intensity med med wk

Assignment CH2 & CH3 deformation CH3 deformation CH2 rocking

Alkanes 28503000

Alkenes 30203100 16301680

med var

=C-H & =CH2 (usually sharp) C=C (symmetry

880-995 780-850 675-730

str med med

=C-H & =CH2 (out-of-plane bending) cis-RCH=CHR

str

reduces intensity)

19002000 Alkynes 3300 21002250 str var

C=C asymmetric stretch C-H (usually sharp) CC (symmetry reduces intensity) 600-700 str C-H deformation

The purpose of this experiment is to identify 12 compounds (compound A to compound L) by using the knowledge of UV-Vis and IR Spectroscopy.
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PROCEDURE
A) IR spectroscopy

1. Before using the IR machine its tray must be washed properly using acetylene . 2. Then, the scan icon is clicked on the monitor . 3. Drop the unknown solution A continuously to the machine tray until the results appear on the monitor of the computer. 4. Save your results the way instructor told you to save it. 5. Repeat step 1 to 4 for solution B to L B) UV-vis spectroscopy

1. For using the UV-vis spectroscopy first couvettes are washed by using acetone in the fume cupboard 2. The couvettes are inserted into the cuvette holder inside the sample compartment according to its beam paths. The sample compartment was closed. The process is started. Then, one of the cuvettes was removed from the sample compartment before the experiment was preceded for reference. Then, the cuvette that had been removed was cleaned using acetone again and evaporated in the fume cupboard 3. One drop of sample A is mixed thoroughly with sample solvent in a sample bottle .Then insert it into dry cuvette and place it into sample compartment. Closed the sample compartment and recorded the result. 4. The results obtain are save for further analysis. 5. Repeat step 1 to 4 for solution B to L

RESULTS
ABC A: CH3CH2OH (Ethanol) B: CH3CH(O) (Ethanal) C: CH3COOH (Ethanoic Acid) A+CD A: CH3CH2OH + C: CH3COOH D: CH3CH2OC(O)CH3 (Ethyl Ethanoat) GHI G: C6H12 (Benzene) H: C6H11CH3 (Toluene) I: C6H11COOH (Benzoic Acid) A+J K CH3CH2OH + (Bromoethane) C2H6 (Ethane) R eFrom UV-VIS spectroscopy and FTIR, the data collected is analyzed to identify the reaction above: From UV-VIS experiment, the reference solvent use gives the spectra as below:

0.01 0.00 -0.01 -0.02 -0.03 -0.04

A
-0.05 -0.06 -0.07 -0.08 -0.09 200 250 300 350 400

nm

Reference solvent spectra (UV-VIS)

101.0

95

3750.55 1541.56

90

85

1456.54

1088.70

880.95

80

2831.93 2943.24

75

70

3328.33 585.74 525.22

65 %T 60

55

50

45

40

35

30 27.0 4000.0 3600 3200 2800 2400 2000 1800 cm-1 1600 1400 1200 1000 800 600 515.0

IR-spectra for compound A

0.01 0.00 -0.01 -0.02 -0.03 -0.04

-0.05 -0.06 -0.07 -0.08 -0.09 -0.10 -0.11 200 250 300 350 400

nm

UV-VIS spectra for compound A For compound A, the spectra from FTIR experiment shows that there are wide broad band at 3328.33 cm-1 that reflects that the functional group of OH (Hydroxyl) existed. The other existing peak is located at 2943.11cm-1 which indicates the presence of C-H bond. From UV-Vis spectra, compound A does not show any absorption. For reaction of compound A with PCC in CH2Cl2 give us compound B. Compound B when reacted with CrO3 in sulphuric acid H2SO4 give compound C. PCC is mild oxidizing agent. When primary alcohol which is compound A (ethanol) reacted with PCC, aldehyde will be formed. Specifically ethanal is formed from the reaction. When it is oxidize further, compound C is formed. Actually compound C should be a carboxylic acid but in this case, ethanoic acid was formed.

101.0

95

3741.88

90
1541.51 1522.31 2631.02 532.00 525.24

85

80
1051.94

75

2990.16 1360.11

70

1756.99

1012.96

65
927.99 889.14

60 %T 55
1408.59

606.59

50

45
626.48

40

35

1287.85

30

25

18.6 4000.0 3600 3200 2800 2400 2000 1800 cm-1 1600 1400 1200 1000 800 600 515.0

IR-spectra for compound C

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1.6 1.4 1.2 1.0

0.8 0.6 0.4 0.2 0.0 200 250 300 350 400

nm

UV-VIS spectra for compound C

From experiment conducted, peaks can be seen developed in the IR absorption spectra. The peak at 2990cm-1 and 2631.02cm-1 in medium intensity indicate the existence of C-H group. For 1756.99 cm-1 absorption in strong intensity, it can be said that C= O group presence. Strong peak intensity at 3741.88cm-1 shows that OH group present in the compound C. From UV-Vis spectroscopy, compound C absorb at max=214.7nm with intensity of 1.669. This shows that there are bond systems in this compound and it shows that compound C is ethanoic acid. Compound D is formed when compound C reacts together with compound A in HCl. Based on theory, when ethanol (primary alcohol) reacted with ethanoic acid, ester will be form. Compound D is also known as ethyl ethanoate.

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108.8 105

100

95
3747.80 1541.75 786.21 573.89 544.01 532.11 524.65

90

85
2984.74 1447.73 938.12 1097.52 847.06 634.22

80

75
607.47

70

65 %T 60

55
1372.76

50

45

40

35

30
1043.57

25
1233.49 1736.54

18.6 4000.0 3600 3200 2800 2400 2000 1800 cm-1 1600 1400 1200 1000 800 600 515.0

IR-spectra for compound D

1.2 1.1 1.0 0.9 0.8 0.7

0.6 0.5 0.4 0.3 0.2 0.1 0.0 200 250 300 350 400

nm

UV-VIS spectra for compound D

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Absorption at 2984.74cm-1 from IR spectra for compound D, refer to CH group. Absorption at 1736.54cm-1 shows the existence of C=O group. The other absorption obtained is 1043.57cm-1, this refer to C-O group. From UV-Vis experiment, compound D shows max= 214.11nm with intensity of 1.268. While conducting the experiment, this compound smells like fruity fragrance showing us that this compound is an ester. Specifically it is ethyl ethanoate.

108.8 105

100

95
3750.46 1771.81 1698.73 1541.61

90

85

1317.29 1247.39 2884.77 3328.55 1456.62 1380.08

80

75
2973.83

714.05 664.51

526.63

70

65 %T 60
879.84 1087.66

55

50
754.75

45

40

35
1046.29

30

25

19.3 4000.0 3600 3200 2800 2400 2000 1800 cm-1 1600 1400 1200 1000 800 600 515.0

IR-spectra for compound I

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10 9 8 7 6

5 4 3 2 1 0 200

250

300

350

400

nm

UV-VIS spectra for compound I

From IR absorption of compound I at 3328.55cm-1, wide broad band indicate OH group. Other absorption shows that 1456.62cm-1 indicate aromatic ring. The absorption of aromatic ring is shown in medium intensity. Absorption 1771.81cm-1 shows that the existence of C=O functional group. From UV-Vis spectra for peaks were obtained. The first one is at max=272nm at intensity of 1.201. The second peak is located at max=232nm with intensity of 10. The third one is at max=224.01nm with intensity of 5.137. The last peak is indicated at the max=220.08nm with intensity 4.393. All these peaks shows the presence of benzene ring. From the reaction given, compound G reacted with FeCl3 in CH3Cl giving the compound H. Compound H then reacted with KMnO4 and followed by hydrolysis to give compound I. From all the results obtained, compound I can be identify as Benzoic acid. Compound H is toluene and compound G is benzene.

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120.0 115 110 105 100 95

3749.91 2868.08 2924.46 2978.90 613.61 648.56 739.39 630.70 705.50

2043.52 2021.05

1698.61 1757.01 1670.24

1521.89 1541.51

1061.94

894.43 875.14

90 85 80 75 70 65 60 %T 55 50
557.71 1241.67 575.08 548.94 958.72 1377.86 1442.63 844.91 695.95 811.45 675.07 768.54 655.34 526.48 640.17 621.91 605.85 588.94 567.89 598.97 541.38

45 40 35 30 25 20 15 10 5 0.0 4000.0 3600 3200 2800 2400 2000 1800 cm-1 1600 1400 1200 1000 800 600 515.0

IR-spectra for compound J

10 9 8 7 6

5 4 3 2 1 0 200

250

300

350

400

nm

UV-VIS spectra for compound J

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For the next compound that is compound J, the IR absorbance spectra shows peak at 557.71cm-1 that indicates to C-Br group. This show that compound J is an alkyl halide. The other peak that exists is located at 2924.46cm-1. This peak corresponds to C-H group. From the reaction given, compound J reacted with compound A in NaH/THF solution to form compound K.

120.0 115 110 105 100 95 90 85 80 75 70 65 60 %T 55

2296.96 2034.18 2010.80 1989.11 1964.99 1647.08 1699.89 1748.94 646.06 1542.34 674.25 697.18 869.33 902.95 890.37 685.41 881.58 821.97 720.63 813.77 730.00 767.79 707.07 775.18 753.21 712.95 665.46 639.40 567.01 795.06 936.49 835.84 843.10 630.45 971.13 544.49

50 45

3749.81

1450.68 1350.63

40 35 30

2944.72 1381.69 2869.88 1252.47 2976.97 1074.17 571.54 598.46 617.47 591.91

25 20

557.51

15 10 5
1119.45 539.04

0.0 4000.0 3600 3200 2800 2400 2000 1800 cm-1 1600 1400 1200 1000 800 600
584.29

515.0

IR-spectra for compound K

532.97 578.87

551.55

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1.8 1.6 1.4 1.2 1.0

A
0.8 0.6 0.4 0.2 0.0 200

250

300

350

400

nm

UV-VIS spectra for compound K

IR spectra for compound K, shows peak at 2869.88cm-1 corresponds to C-H group. Another obvious peak is at 1119.45cm-1 which correspond to C-O group.Only one absorption occurs for UV-Vis spectroscopy result for compound K located at max=270.85nm with intensity 1.833. The peak may refers to the lone pair that exists in compound K. Diethyl Ether will be produce when Ethanol reacted with Ethyl Bromide (alkyl halide), ed. Thus, compound J should be Ethyl bromide while compound K is the resulting compound that is Diethyl Ether.

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DISCUSSION
Based on our objective, we need to identify the organic compounds of some sample by using UV-Vis and IR spectroscopy. We had been used 6 sample, thats is compound A,compound C,compound D, compound I, compound J, compound K. From IR spectroscopy result some absorption band occured that showned functional group for that organic compound. Its quite difficult to determine the compound based on their functional group because we need to make sure the structure. Different structure can give diffferrent result of compounds. For compound A, from IR spectra and UV-Vis , the absorption band shown that it had a functional group of H group, O-H group, C-CH3 group and C-O bond. Based on our prediction, the possible compounds is ethanol because ethanol had C-CH3 group,O-H group and C-O bond. Ethanol (CH3CH2 OH) didnt have many branch and can oxidized to become aldehyde when reacted with PCC. As we known PCC is weak oxidizing agent and can change primary alcohol became aldehyde. Ethanol is primary alcohol and when reacted with PCC, it can change into ethanal. For compound B it had strong absorption band at range of 1650 cm-1 to 1750 cm-1 and it presence of carbonyl compounds functional group. Based on our prediction, compound B is aldehyde because when primary alcohol reacted with PCC with presence of CH2CI2, it will become aldehyde. So, the possible structure is ethanal (CH3 -CH =OH). Based on our reaction, when compound B (aldehyde) reacted with CrO3 with presence of H2SO4 it can be oxidixed to became carboxylic acid. Based on our experiment using IR spectra and UV-Vis we determine the absorption band occured showned three functional group, that is Carboxylic Acid (O-H) group, Carbonyl compound (C=O) and (C-CH3)group. Its absolutely showned that compound is ethanoic acid because had functional group of carboxylic acid. When alcohol reacted with carboxylic acid, it can give ester compound by the presence of HCI . For compound D, based on absorption band, it had a fuctional group of -COCH3 group and Ester, -CO-O- group. The possible structure for compound D is Ethyl ethanoate. Other compounds that we need to determine are compound (E,F,G,H,I,J,K,L). For compound G, when it reacted with CH3CI and FeCI3 the reaction be aromatic chlorination by electrophilic substitutions of benzene ring. So, possible structure for compound G is benzene ring. By IR spectra and UV-Vis, the absorption band we get is presence of aromatic ring and arene group. Only benzene ring can make electrophilic substitutions and by the reaction, possible structure for
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compound H is methylbenzene. It also had absorption band that presence of aromatic ring, arene and C-H bond by plane deformation. For compound H, the possible structure is methlbenzene by reaction of benzene by electrophilic substitution. For compound I, when methlbenzene oxidized with KmnO4 with presence of H2O, the product occured is Benzoic acid. This reaction is called oxidation of alkylbenzene side chain. CH3 will change into COOH. For IR spectra, absorption band for compound J identify that had functional group of Arene, CH bond, and Alkene, C=C bond. Its maybe ring structure because had -C=C- bond, C-H out-ofplane deformation that basic structure of ring . So, the possible structure is cyclohexene. When ethanol reacted with cyclohexene with presence of NaH and THF, structure of K occured. NaH and THF will break double bond of cyclohexene and give hexane structure. For compound L, from absorption band we get, the possible structure is dimethyl ether because it have COCH3 bond and (CH2 and CH3 ) bonds. For compounds E and F, its quite difficult to determine the compound because compound E has CH2 bond, , C=O bond and O-H bond. Its maybe cause of many branch at compound E and its were combining of alcohol, carboxylic acid and alkane. For compound F, the possible structure is Methanediamide because it had functional group of CONH2 group and -NH2 group. -NH2 group will give amide group because presence of nitrogen. Based on our result of IR spectra absorption band, our experiment achieve the objective but maybe had some mistakes occured. The bottles maybe not clean properly by acetone, pipet use for more than one compound and some parrallax error that cant be avoid . IR specta and UV-Vis spectroscopy is good method to determine an organic compounds by looking at band absorption.

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CONCLUSION

As the conclusion, the experiment is successful and the objective of the experiment is achieved. Our experiment is followed the theory of UV-Vis and IR Spectroscopy. From the results, compound A is alcohol group. We have managed to identify the 12 compounds and this make this experiment to be considered successful. Compound A is ethanol, compound B ethanal, compound C is Ethanoic Acid, Compound D is Ethyl Ethanoate , compound E is Aspirin(AcetylSalicylic Acid), compound F is Diamide Ketone, compound G is Benzene, compound H is Toluene, compound I is Benzoic Acid, compound J is Bromoethane , compound K is Diethyl ether, compound L is Hexane. From the experiment, what we have learned is how to conduct the UV-Vis and IR spectroscopy. Besides, we have gained the knowledge in read the UV-Vis and IR spectroscopy graph.

REFERENCES
A) Books i. ii. Williams D.H and Fleming Ian, 2008, Spectroscopic Methods in organic Chemistry, Sixth Edition London, McGraw Hill. John McMurry, 2004, Organic Chemistry, 7th edition, Thompson Book/Scole.

B) Internet i. ii. iii. iv. NIST Chemistry Web Book. http://webbook.nist.gov/chemistry/ First accessed 11/00. Wikipedia http://www.wikipedia.com http://www.files.chem.vt.edu/chem-ed/spec/uv-vis/uv-vis.html http://www.prenhall.com/settle/chapters/ch15.pdf

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